Stereoselectivity of formation of monoterpene - Amino acids hybrid molecules in the reaction of monoterpene nitroso chlorides with alpha-amino acid derivatives

Stereoselectivity of formation of monoterpene - Amino acids hybrid molecules in the reaction of monoterpene nitroso chlorides with alpha-amino acid derivatives Full article

Journal

Steroids
ISSN: 0039-128X , E-ISSN: 1878-5867

Output data

Year: 2017, Volume: 117, Number: SI, Pages: 112-119 Pages count : 8 DOI: 10.1016/j.steroids.2016.09.016

Tags

Amino acids; (+)-3-Carene; (-)-alpha-Pinene; Nitroso chlorides; Diastereoselectivity

Authors

Marenin K.S. ¹ , Gatilov Yu.V. ¹ , Agafontsev A.M. ¹ , Tkachev A.V. ^1,2

Affiliations

1	(Данные Web of science) NN Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Dept Nat Sci, Novosibirsk 630090, Russia

Reaction of nitrosochlorides of natural monoterpene hydrocarbons (+)-3-carene and (-)-alpha-pinene with L-amino acids and their methyl esters results in stereoselective formation of terpene-amino acids hybrids, which belong to the series of alpha-substituted amino oximes. The reaction with an excess of racemic DL-amino acids and their derivatives induces partial resolution of the amino acid components and formation of the diastereomeric mixtures of the terpene-amino acids hybrids, with diastereomeric excess varying from 0 to 100%. (C) 2016 Elsevier Inc. All rights reserved.

Marenin K.S. , Gatilov Y.V. , Agafontsev A.M. , Tkachev A.V.
Stereoselectivity of formation of monoterpene - Amino acids hybrid molecules in the reaction of monoterpene nitroso chlorides with alpha-amino acid derivatives
Steroids. 2017. V.117. NSI. P.112-119. DOI: 10.1016/j.steroids.2016.09.016 WOS Scopus РИНЦ

Published print:

Jan 1, 2017

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Elibrary	29466566
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